3-Nitrobenzaldehyde → 3-(1-Benzylpyrrolidin-3-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 27067

反応式

HRID 27067 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[CH2:12]([N:19]1[CH2:23][CH2:22][CH:21]([O:24][C:25](=[O:30])[CH2:26][C:27]([CH3:29])=O)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:31][O:32][C:33](=[O:38])/[CH:34]=[C:35](\[NH2:37])/[CH3:36]>C(O)(C)C.C(Cl)(Cl)Cl>[CH3:31][O:32][C:33]([C:34]1[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:26]([C:25]([O:24][CH:21]2[CH2:22][CH2:23][N:19]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:20]2)=[O:30])=[C:27]([CH3:29])[NH:37][C:35]=1[CH3:36])=[O:38]

参加物

6

反応物 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 136528121-Benzyl-3-acetoacetoxypyrrolidine

生成物 1

HCID 22963-(1-Benzylpyrrolidin-3-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate収率 69.2%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 6212Chloroform溶媒2 回

実験手順

In 5 ml of isopropyl alcohol were dissolved 1.5 g (0.01 mole) of 3-nitrobenzaldehyde, 2.6 g (0.01 mole) of 1-benzyl-3-acetoacetyloxypyrrolidine, and 1.3 g (0.01 mole) of β-aminocrotonic acid methyl ester and then the solution was refluxed for 8 hours. The solvent was distilled off under reduced pressure, the residue obtained was dissolved in a small amount of chloroform, and the solution was applied to silica gel column chromatography (column diameter 1.5 cm, height 20 cm, and about 200 ml of chloroform was used as the eluant). The eluates were collected and concentrated to give 3.4 g of oily 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-(1-benzylpyrrolidin-3-yl)ester-5-methyl ester.

後処理

  1. temperaturethe solution was refluxed for 8 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue obtained
  4. customThe eluates were collected
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-937b1a4b3c184e5f9777790382258d4d
出典データセット
uspto-grants-1980_09
特許番号
US04220649

関連ノート

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